The Solution Conformation of Lactal and ITS Hexa-O-Acetyl Derivative |
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Authors: | Alfonso Rivera-Sagredo Jesús Jiménez-Barbero |
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Institution: | Grupo de Carbohidratos , Instituto de Química Orgánica , C. S. I. C., Juan de la Cierva 3, 28006, Madrid, (Spain) |
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Abstract: | Abstract The conformation of lactal (1) in D2O and DMSO-d6 has been investigated by employing NMR techniques and molecular mechanics calculations. The glucal ring shows a 4 H5 conformation in deuterium oxide and DMSO-d6. In contrast, the glucal ring of the hexa-O-acetyl derivative (2) in CDCl3 can be described as an equilibrium between the 4 H5 and 4 H5 forms. The disaccharide 1 has a restricted flexibility with the Φ angle oscillating about -105 ± 30° and the Ψ angle varying about -145 ± 30°. Compound 2 shows a similar conformational behaviour. |
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